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(2Z,2′Z,4E,4′E)-4,4′-(Cyclohexane-1,2-diyldinitrilo)dipent-2-en-2-ol
A new tetradentate chiral Schiff base ligand, C(16)H(26)N(2)O(2), has been synthesized by the reaction of acetylacetone with (1R,2R)-(−)-1,2-diaminocyclohexane. Both of the molecules in the asymmetric unit are of the same chirality (R configuration), since the absolute configuration was determi...
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2008
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961254/ https://www.ncbi.nlm.nih.gov/pubmed/21202336 http://dx.doi.org/10.1107/S160053680800977X |
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author | Li, Xiu-Zhi Qu, Zhi-Rong |
author_facet | Li, Xiu-Zhi Qu, Zhi-Rong |
author_sort | Li, Xiu-Zhi |
collection | PubMed |
description | A new tetradentate chiral Schiff base ligand, C(16)H(26)N(2)O(2), has been synthesized by the reaction of acetylacetone with (1R,2R)-(−)-1,2-diaminocyclohexane. Both of the molecules in the asymmetric unit are of the same chirality (R configuration), since the absolute configuration was determined by the starting reagent (1R,2R)-(−)-1,2-diaminocyclohexane. The six-membered cyclohexane ring is in a chair conformation, and the substituents are equatorial in the most stable conformation (trans-cyclohexyl). At the ring substituents, large conjugated —C=N—CH=C—OH systems exist, resulting from the original ketone converted into the enol form. With H atoms excluded, the atoms of each substituent lie in the same plane. The two molecules in the asymmetric unit have almost the same structure, with slight differences in the torsion angles between the substituents and the cyclohexane ring; the corresponding N(1)—(C—C—C)(cyclohexane) torsion angles are −177.2 (3) and 179.3 (4)° in one molecule and −176.5 (3) and 178.4 (4)° in the other. Two intramolecular O—H⋯N hydrogen bonds exist in each molecule. |
format | Text |
id | pubmed-2961254 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29612542010-12-30 (2Z,2′Z,4E,4′E)-4,4′-(Cyclohexane-1,2-diyldinitrilo)dipent-2-en-2-ol Li, Xiu-Zhi Qu, Zhi-Rong Acta Crystallogr Sect E Struct Rep Online Organic Papers A new tetradentate chiral Schiff base ligand, C(16)H(26)N(2)O(2), has been synthesized by the reaction of acetylacetone with (1R,2R)-(−)-1,2-diaminocyclohexane. Both of the molecules in the asymmetric unit are of the same chirality (R configuration), since the absolute configuration was determined by the starting reagent (1R,2R)-(−)-1,2-diaminocyclohexane. The six-membered cyclohexane ring is in a chair conformation, and the substituents are equatorial in the most stable conformation (trans-cyclohexyl). At the ring substituents, large conjugated —C=N—CH=C—OH systems exist, resulting from the original ketone converted into the enol form. With H atoms excluded, the atoms of each substituent lie in the same plane. The two molecules in the asymmetric unit have almost the same structure, with slight differences in the torsion angles between the substituents and the cyclohexane ring; the corresponding N(1)—(C—C—C)(cyclohexane) torsion angles are −177.2 (3) and 179.3 (4)° in one molecule and −176.5 (3) and 178.4 (4)° in the other. Two intramolecular O—H⋯N hydrogen bonds exist in each molecule. International Union of Crystallography 2008-04-16 /pmc/articles/PMC2961254/ /pubmed/21202336 http://dx.doi.org/10.1107/S160053680800977X Text en © Li and Qu 2008 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Li, Xiu-Zhi Qu, Zhi-Rong (2Z,2′Z,4E,4′E)-4,4′-(Cyclohexane-1,2-diyldinitrilo)dipent-2-en-2-ol |
title | (2Z,2′Z,4E,4′E)-4,4′-(Cyclohexane-1,2-diyldinitrilo)dipent-2-en-2-ol |
title_full | (2Z,2′Z,4E,4′E)-4,4′-(Cyclohexane-1,2-diyldinitrilo)dipent-2-en-2-ol |
title_fullStr | (2Z,2′Z,4E,4′E)-4,4′-(Cyclohexane-1,2-diyldinitrilo)dipent-2-en-2-ol |
title_full_unstemmed | (2Z,2′Z,4E,4′E)-4,4′-(Cyclohexane-1,2-diyldinitrilo)dipent-2-en-2-ol |
title_short | (2Z,2′Z,4E,4′E)-4,4′-(Cyclohexane-1,2-diyldinitrilo)dipent-2-en-2-ol |
title_sort | (2z,2′z,4e,4′e)-4,4′-(cyclohexane-1,2-diyldinitrilo)dipent-2-en-2-ol |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961254/ https://www.ncbi.nlm.nih.gov/pubmed/21202336 http://dx.doi.org/10.1107/S160053680800977X |
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